


The Proposition

by silly_mortal



Category: The Time of Your Life - Saroyan
Genre: F/M, Loss of Virginity, Prostitution
Language: English
Status: In-Progress
Published: 2020-09-08
Updated: 2020-09-11
Packaged: 2021-03-06 21:06:28
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 6,862
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26355427
Author URL: https://archiveofourown.org/users/silly_mortal/pseuds/silly_mortal
Summary: Kitty gets a business proposition."Too many things have happened to me." ~ Kitty Duval
Relationships: Kitty Duval/Original Character
Kudos: 8





	1. Chapter 1

**Author's Note:**

> This one is two parts, but maybe three. I wasn't going to write about the actual 'proposition', but I think I set myself up with the last line. We'll see. I marked it as 'mature' because she's a prostitute and I don't know the rules, but there's no sex or violence or anything. I just didn't know which rating is best to use.
> 
> This story is set between the first one I wrote and when we actually meet her in The Time of Your Life (maybe two years before). Kitty has hardened some. She is rid of Charlie and has had a different relationship that I mention in this story. While she briefly thinks about having been hurt in the past, it's not graphic and nothing bad happens to her in this story.
> 
> Kitty's Timeline (so far)
> 
> The Ring  
> Grandfather  
> The Proposition  
> A Series of Questions
> 
> I doubt anyone is on here looking for The Time of Your Life but, if you are and run across this, please let me know if there are any mistakes. I don't have anyone to proofread for me and I myself am the laziest person on the planet.
> 
> As always, Patti LuPone's Kitty is my Kitty. (As I read it, it sounds like she and I are a couple and we share a cat. Or it's a euphemism for... Either way, we share a Kitty.)

Winter, 1938

Kitty stood on the corner, scanning the area. Normally, when she was working, she didn’t have to wait long before a customer happened by but she was not in her usual spot today. A detective had been sniffing around last week, trying to round up as many of the working girls as he could, and it had spooked her. She had managed to avoid him but she changed her location, just in case he showed up again. If she were smart, she wouldn’t work for a few days, until the cop moved onto a new place, but she couldn’t afford that. Things had been slow lately and she hadn’t anything to eat for two days. She had been drinking a lot of water, to keep her stomach from growling, but she was starting to feel lightheaded. 

She was debating about whether to go down to the harbor or to the business district. They were equal distance from here, which was important because she would have to walk it, since she didn’t have any money for the streetcar. It was midday on Saturday, so finding a businessman would be difficult, unless they were there to get a bit of extra work done. Businessmen were cleaner than the sailors, but the chances of her finding a customer were greater at the harbor. Still, things had been so slow that she couldn’t afford to go to the doctor if they passed something on to her, so she decided to think about it for a moment longer.

Just as Kitty was about to head toward the harbor, she noticed a man peeking around the corner, staring at her. She had seen him walk by twice earlier, but he didn’t seem interested in her at the time. Now he did. She was able to get a good look at him and noticed that he wasn’t a man at all, but more of a boy. A teenager, maybe. She had been with some soldiers who were young, but she didn’t think they were this young.

Kitty put on her sweetest smile, the one that worked on all the young ones. She really needed to work.

“Are you going to stare at me all day or are you going to talk to me?”

The boy flushed red and looked away, embarrassed at being caught.

“I’m sorry, ma’am. I didn’t mean to stare.”

She balked, but didn’t let it show. Ma’am? She had just left her teen years and was already considered a ma’am. If she was starting to age on the outside as much as she had on the inside, she really needed to get out of this business.

“Is there something you’d like to ask me? I won’t bite,” she added softly, trying her best not to frighten him away.

He looked at her, nervously.

“Um, yes…. Are you a… a…?”

“Streetwalker?”

“Oh, I wasn’t going to use that word. I was going to say prostitute or working girl, but I didn’t want to offend you.”

“It’s not offensive when it’s the truth. But yes, I am... Is there something you wanted?”

Kitty turned toward him, so he could get a good look at her. She was wearing a dark green dress that fit her like a glove, displaying every curve but not enough to be considered vulgar. She had gotten several compliments on it, how it brought out the auburn tones of her dark hair and how stark it was against her porcelain skin. It was made of a silky material looked so soft that a person would have to will themselves to not reach out and touch it. That was exactly the effect she was going for today and, from the look on the young man’s face, it seemed to be working.

As she looked at him, she sized him up. He was tall, maybe a foot taller than her, with round blue eyes. He was wearing a white button up shirt and dark slacks. Very young and clean cut. She hoped he wanted her. The young ones were always quick and always grateful. They didn’t usually think to tip, but they also didn’t linger afterwards, wanting to get as much time out of her as possible without paying for it.

“I was wondering if I could talk to you about a business proposition,” he said, nervously.

“Well, I _am_ open for business. Do you want to come up to my room? I don’t live far from here.”

“Oh, not that… exactly. I mean, yes that, but in a different way. Something you’ve probably not been asked before.”

Kitty sighed and stared at him, trying to be tolerant.

“There isn’t anything I haven’t been asked before. There is nothing new in this business.”

The boy dropped his eyes to the ground, embarrassed that he seemed to have offended her. His face suddenly brightened.

“Would you like to get something to eat? With me, I mean?”

Kitty’s stomach immediately growled and she prayed that he didn’t hear it.

“I don’t accept food as payment,” she said. “It’s cash only.”

“That’s not what I mean. I was thinking that maybe we could have a meal and, while we’re eating, I could tell you about my proposition. If you agree to it, fantastic. If not, we just had a nice lunch and you can go your way and I’ll go mine. I’m inviting you and it’s my treat. I wouldn’t expect you to pay.”

Kitty hesitated a moment. She was hungry, but she hadn’t shared a meal with anyone for… Well, since the night before William, her husband of only ten days, had died four months before. 

“… unless you have plans. A date or something.”

Kitty looked at him, amused.

“I don’t have a date.”

The boy smiled and clapped his hands together.

“Good, then let’s go. I don’t know the area. Do you? What are you craving? There has to be a restaurant somewhere nearby.”

“There’s a diner around the corner.” 

“Fantastic! Lead the way. Ladies first….” he gestured.

A shy smile crossed her face, as she started walking in front of him. It had been a very long time since anyone had called her a lady.

They settled in a booth at the restaurant and the waiter brought them over some menus. He winked at Kitty, while taking her drink order. She hated running into former customers when she wasn’t actually working. It reminded her that she could never escape what she was, not even for a moment. However, she didn’t want to alienate someone who could just as easily choose a different girl to give his money to, so she smiled back at him.

“I’m Jimmy.”

“Kitty,” she said, while looking at her menu.

“It suits you. You look like a Kitty. I mean... because the name is pretty and you’re pretty, not that you look like a cat. Cats are beautiful animals though. They have such big eyes-”

Kitty lifted her eyes to look at him from over the menu. She was glad she was able to hide her smirk behind it. He was so nervous.

“Thank you,” she said.

When the waiter brought over their sodas, Kitty ordered a cheeseburger and fries, with the works. After Jimmy had placed his order, she suddenly asked the waiter to leave off the onions.

“Do you not like onions?” Jimmy asked, as the waiter walked away.

“I do, but it’s not good for the job… Men don’t want to kiss, or do anything else, with girls who smell like onions,” she explained, when he looked confused.

Jimmy blushed and looked down. 

“Are you old enough for this… _proposition_ of yours?” she asked.

When he looked up, he saw her staring at him, curiously.

“I’m 18,” he said. “I’m in my senior year at Strathmore Academy.”

Kitty nodded.

“I can prove it to you, if you want,” he said, reaching into his pocket. “I have my ID.”

“That's not necessary, but I would like to hear your _business_ proposition,” she said.

Jimmy took a deep breath, before speaking. She listened patiently as he told her about the girlfriend he had had for two years, before she broke up with him just two weeks before. He was devastated that she immediately began dating a football player at the school and, according to the school rumor mill, she was already sleeping with him when she had never let Jimmy do more than kiss her.

Kitty nodded, sympathetically, letting her mind wander for a moment, as he spoke. When you were young, before your first introduction to real life, everything felt like the end of the world. He was clearly hurt by the girl’s actions, but didn’t seem to understand what true devastation was. Kitty wished that her first boyfriend had merely left her to date someone new, instead of forcing her to go to bed with strangers for money, so that he had money to gamble he didn’t have to get a job. She shook the image out of her head and went back to listening to what he was saying.

“So, the dance is this Saturday and I really need a date, especially one as pretty as you. What do you think?”

“What would this _date_ include exactly?”

“Well, I’d like it to look real… as if you really like me and aren’t just paid to be there... I’d pick you up- I have a car. We’d go out to dinner, either before or after the dance. I’d pay for everything, your dress and to have your hair done. We’d go wherever the kids are going after that, probably to Lookout Point, if that’s ok. It’s a make-out spot.”

Kitty nodded, understanding. Chicago had also had a make-out spot, when she was going to school there.

“I assume this date will involve a _happy_ ending?”

Jimmy turned beet red and looked away, embarrassed.

“I’m not judging,” Kitty said, quickly. “I just need to know the details, so that I can come up with a price.”

“Yes, please,” he murmured, still not looking at her.

“And you want that to take place in the car at Make Out Point, where the other kids are?”

Jimmy looked at her, quickly.

“Oh no! I don’t want to be disrespectful, at all. I mean, I’d like to let them see me kiss you there and maybe make it _appear_ that that’s what we’ll be doing when we leave, but I wouldn’t ask you to do something like that around other people…. But it _is_ prom night and I’d like it to be special, so…. I would like to end the evening with...” he trailed off, unable to say the words.

Kitty nodded, trying to calculate what to charge in her head. Two dollars was the going rate for sex, but that generally only took 15-30 minutes, depending on what the customer wanted. This would be all evening, but he only wanted to do it once, as well as some necking. She couldn’t charge more than a dollar for kissing, three if he decided that he wanted some form of sex in the car because that could get her arrested. Plus, he would be taking her out for dinner and a dance. Kitty loved to dance and it had been so long since she had done so. She was aware it wasn’t a real date, that it was a job, but it would be like a dream. She had been starved for one day that seemed like normal life again, not to mention an actual conversation with someone. She figured she could charge him five dollars for the whole evening and if he didn’t want to pay tha-

“A friend of mine said that it’s $2, normally, for a…. lady. I was thinking $10 for the night, if that’s enough, plus I’d buy your dress and shoes and whatever else you need. Is that too little? I don’t know what you charge for the whole evening.”

Kitty was in the middle of taking a sip of her soda, when he said the price, and immediately began coughing and sputtering. 

“Are you ok?” 

She nodded, while continuing to cough. Ten dollars… She couldn’t remember the last time she had ten dollars at one time. If she used it correctly, she could have a nest egg again and not have to go hungry on days business was slow. She wouldn’t have to walk the streets until she got blisters on her feet, just trying to find one john. She could-

Kitty suddenly realized that Jimmy was sitting beside her in the booth, patting her back and offering her a glass of water. She took a sip and waited until her breathing returned to normal.

“Are you ok?” he asked, again. “Did I insult you with the price? Just tell me how much more it would be and I’ll pay it.”

“No, the price was fine. I think I just swallowed wrong - it went down the wrong pipe. I’m ok now,” she smiled.

Thankfully, the waiter was bringing them their food then, so they didn’t have to sit there, awkwardly, until Jimmy returned to his own side of the booth. Kitty had to keep herself from scarfing down everything on her plate. The last thing she wanted to do was to appear to have bad manners and do something that might make her appear less attractive to a customer. 

They didn’t speak for awhile, as they began eating. She was already trying to figure out how she could find a ladylike way to box up half of her meal to take home. She might be earning ten dollars on Saturday but, until then, she had no idea how business would be, so she would have to make it last.

Jimmy cleared his throat.

“There is one other thing...” he said, looking at her.

Kitty froze and looked at up him. She knew it was too good to be true. There is no way anyone would pay her five times her going rate for one roll in the hay and some necking. She braced herself for whatever filthy thing she was going to have to do, in order to earn that money, and with how many people.

Jimmy leaned forward and lowered his voice to a whisper.

“I’ve never been with a girl before… and I’d like my first time to be before the dance. Before Saturday, I mean. If that were to be my first time, I’d be nervous all night, wondering what it’s going to be like and I won’t be able to enjoy the dance.”

Kitty released the breath she had been holding. Was that it? He wanted an additional lay? For ten dollars all at once, she would have let him spend the entire weekend in her bed, doing her as often as he wanted. This boy had no idea how desperate she was and what all she’d be willing to do for that money. She imagined that he had never known what it was like to go hungry.

“So...” she said, slowly. “You want to do it before we leave on Saturday and then again, after we get back?”

“That sounds really nice but what I was actually thinking is that, maybe, we could do it the first time sometime before Saturday. I’ll already be a bundle of nerves on Saturday, I don’t want to make it worse. I’ll pay you for that too, of course. I’m not trying to include it in the Saturday price.”

“Ok… So, when would you like to do this?”

“Whenever you have time, I suppose.”

“I have time now.”

Jimmy looked at her, startled. He blushed again. He blushed often, she noticed. His fair skin betrayed him by flaring up every time he got embarrassed.

“But... we’re still eating,” he said.

“I meant afterwards.”

Did he think she was going to push the food onto the floor and take him there, on the table? The poor kid. He had no idea about anything. She needed the money and knew she had to get him to commit now. Anything could happen before Saturday - he could make up with his girlfriend or decide not to go to the dance, but she needed a customer as soon as possible.

“Oh… Ok, that’s fine. I mean, if that’s ok with you…”

“Well, I don’t have a date or anything,” she teased.

This caused Jimmy to smile, as well. Kitty bit her lower lip, in response. It was a nervous habit of hers, something she had done since childhood and not something she did as an attempt to be sexy... but it made him focus on her lips and she noticed that his demeanor changed. Kitty knew she had him then. She deliberately let her teeth drag across her lip, slowly, as she released it.

“Sure! I mean, yes, ok. Whatever works for you,” he said, eagerly.

Kitty continued making eye contact with him, as she took a sip of her soda. She wanted to keep him on the hook but, if she was going to get paid, she sure as hell wanted to finish her meal. She wasn’t full yet.

“Wait, when should we get your dress?” he suddenly asked. “It would be nice if we could do it today, because I’m in school all week and I’d like to know the color, so I can match it with what I’m wearing.” 

“We could do it today, either before… Or _after_ ,” she looked at him, meaningfully. She wanted that two dollars in her pocket as soon as possible. 

“Ok… I guess we should finish eating then.”

Kitty smiled at him. They went back to eating and, as they ate, she stole glances at him. She couldn’t imagine why he hadn’t been with anyone, as of yet. He was young and appeared to be shy, but he seemed like a nice enough boy and was good looking, not that it mattered. She no longer judged men based on attractiveness, but by the likelihood of them either hurting her or robbing her. A man with the face of an angel could beat her up just as easily as a man with a demon’s – and had before, more than once. 

“Hey, I feel like something sweet. Would you like some dessert?” Jimmy asked, while gesturing to the waiter.

Kitty bit her lip again. It had been so long since she had had a treat, but she decided against it. She didn’t want to appear greedy. That would be unattractive and she couldn’t have a john see her that way.

“No, thank you.” 

“Oh, come on… Not even a bowl of ice cream?”

She shook her head, smiling.

“Dessert for the _lady_?” the waiter asked, leering at her.

Kitty looked away, uncomfortably. He knew from experience that she wasn’t a lady.

“A banana split, please, with two spoons,” Jimmy said, “My friend and I are going to share it.”

Kitty smiled at Jimmy as the waiter removed their plates, to make room for their dessert.

“How old are you?’ he asked.

“I just turned 20 last month.” 

“How long have you been doing… _this_?”

“Almost two years. Off and on.” 

“Since you were my age?”

She nodded, expressionless. 

“What do you plan on doing when you get out of school?” she asked, changing the subject.

The last thing Kitty needed was a potential customer to get an inkling that she didn’t like what she did for a living. If they felt sorry for her, they might feel guilty touching her. She couldn’t have that and still manage to make a living.

Jimmy began telling her about his college and future plans, how he was headed to Harvard in the fall and planned to go into business. He told her how he was a trust fund kid and that he got a weekly allowance from his banker father, which is why he had money for their arrangement. They chatted as they shared the dessert the waiter eventually brought and each found that, once their business discussion was concluded, it was easy to talk to the other. 

He asked Kitty where she was from and about her interests. She was careful to make her answers vague and not to reveal too much, but she enjoyed being asked questions and having someone talk to her. It had been such a long time since someone seemed to be interested in her thoughts and feelings. She enjoyed being able to forget what her life was actually like and to be able to feel like a normal person for even a few minutes.

Kitty decided that she liked Jimmy and that she was going to do whatever she could to make Saturday (and maybe tonight) the best night of his life.


	2. Chapter 2

**Summary for the Chapter:**

> Jimmy loses his virginity to Kitty.

After shopping for a dress and accessories for Kitty to wear to the dance, they took a cab to the hotel she rented a tiny room. Over the past few hours, Kitty had spent more time with Jimmy than she ever had with a customer. The normal interaction she had with a john usually consisted of a brief discussion concerning price, a short walk to her room, a quick coupling and then a meek parting of the ways. Of course, she had repeat customers, several of them, in fact. Some of them liked her very much and sometimes attempted to form some sort of relationship with her. She always discouraged it and never gave them any thought one way or the other, even as she was in the middle of the act. Knowing this would be his first sexual experience she somehow felt an enormous responsibility to Jimmy. Actually, she thought, she didn’t know for sure that it would be his first encounter with sex. He had only said that he had never been with a woman before, he hadn’t said a thing about men. 

Kitty glanced over at Jimmy. He was staring out the window and wringing his hands together, nervously. He was no doubt worried about what awaited him when he reached Kitty’s room. She reached over and gently touched his hand with her own. He looked at her, startled.

“Are you ok?” she asked him, softly, so the driver wouldn’t hear.

He smiled, sheepishly, and nodded.

“Just a little nervous.”

“Don’t be,” she whispered, smiling shyly. “I promise I’ll be gentle. Everyone’s first time should be gentle.”

“Was yours?”

He noticed that she didn’t answer him, but instead turned to look out the car window. Before he had a chance say anything further, she was informing the taxi driver that their destination was on the right. 

After exiting the cab, Jimmy paid the driver and then proceeded to follow Kitty into the hotel and up the stairs, carrying her packages that contained her attire for Saturday night. She unlocked the door to the room and stepped inside, Jimmy following closely behind her. 

The room was tiny, but immaculate. There was a small double bed against the wall, with a night stand with a drawer next to it, on one side. A jar of hand cream and a sleeping mask sat on it and Jimmy imagined that she used the mask to block our the morning light which probably poured in. The one window in the room was tiny and to the left of the bed, with a thin white sheet over it that probably did nothing to block out any light but was more for the sake of privacy. The bedding was stark white and there was a small heart-shaped pillow between the two larger pillows. To the right of the bed, there was a small alcove that had a tiny table with a hotplate and a single chair. She must not have many visitors, he thought. Well, none that stayed long enough to share a meal with her. 

There were two small doors in the room, one of which was a closet because the door was ajar and Jimmy could see a few dresses hanging there, as well as one black pair of worn shoes sitting at the bottom. He assumed the other door was a bathroom because Kitty was gone and he heard running water coming from behind it.

The room he slept in at his parents’ home could easily fit four of these rooms in it and this is where Kitty lived every day of her life. She slept here, ate here, probably washed her clothes and herself, all in this tiny room. She had so few possessions, no pictures nor anything that made the room look homey, except for that heart shaped pillow and a tiny vase on the table, that held a plastic pink flower.

Jimmy was trying to figure out where she kept her underthings, when he noticed Kitty had come out of the bathroom. She had taken off her hat and her hair was loose, the dark curls falling just above her shoulders. Without her heels on, she was so tiny. He imagined that her head would just barely reach the bottom of her chin. She was wearing a silk, peach colored negligee and a matching dressing gown, so pale in color that it was only a shade darker than her skin. It had white lace trim and the neckline was nowhere near her neck, but much, much lower.

He drew his eyes up to find Kitty staring at him, startling him.

“Sorry, I was just-”

“It’s small, I know. I don’t need much,”she shrugged, looking around the room.

“How long have you lived here?”

“About four months.”

“Where did you live before that?”

“Somewhere else.”

He blushed again, when he realized that he might be overstepping her boundaries. He felt that, even though they would shortly be undressed, with a part of his body inside her body, he had gotten too personal.

“I’m sorry if I offended you.”

“You didn’t offend me,” she said, simply.

Kitty reached for a red scarf that was hanging in the closet.

“What’s that for?” Jimmy asked, without thinking. “Are you going to tie me up?”

Kitty laughed, involuntarily.

“I hang it on the door so that people know I am with someone. If a… customer comes to the door and sees the red scarf, they know I’m with someone at the moment and they have to come back. If the green one is out there, they know they can knock.”

“What if there is no scarf, like when we came in?”

“That means I am either not home or unavailable.”

Quickly opening the door, she placed the scarf over the doorknob, before closing it again and turning to Jimmy. She looked up at him, expectantly. He shifted, uncomfortably, not knowing what to do. Suddenly, he understood.

“Should I pay you now or after?”

“Now, please.”

He brought out his wallet and fumbled through it. Kitty noticed that his hand was shaking as he handed her the two bills and she found it oddly endearing. She never felt anything for johns, no matter how young or kind they were. It was his fear that made her feel something, she supposed. She knew very well what it was like to be young and afraid.

“Would you like to wash up?” she asked, as she turned and put the money in her purse.

When she turned back around, Jimmy was facing her, holding a small, packaged prophylactic in his hand.

“I have a… a… My friend said that it would be good protection. For both of us.”

She nodded, as he stood there holding it.

“Good. That’s a smart choice.”

They continued staring at each other for a moment.

“I’ll go wash up now,” Jimmy said, rushing into the bathroom.

Once inside, he sighed in relief. He was so nervous that he wasn’t sure what to do with himself. While he had enjoyed the time he and Kitty had spent in the restaurant and out shopping, now he found himself shaking in fear every time she looked his way. 

He looked around the bathroom, which was hardly bigger than a closet. It escaped him how the architect had managed to fit a sink, a toilet and a tiny shower stall in there. On the tray of the sink, there was a small soap that was in the shape of a rose. Inside the shower, there was another one on a small shelf, along with a razor. Jimmy lifted up the soap and smelled it. As expected, it smelled of rose. He wasn’t sure what he was supposed to use to wash up, nor how he felt about smelling like a rose, but it was the only soap in the room. 

After removing his clothes, he stepped into the stall. He used the rose-smelling soap to lather his hands, before washing his genitals and under his arms. Afterwards, he realized that there wasn’t anything to dry off with. He grabbed his shirt and considered using that, but he didn’t know how he’s be able to leave with a wet shirt on and he didn’t know if Kitty would let him wait around until it dried.

“Um… Kitty?”

“Yes?” she answered, from the other room.

“I don’t have anything to dry myself off with.”

“There should be a towel hanging on the door… behind you.” 

Jimmy turned and saw it. He felt stupid for not checking first, but he could barely turn in this small room.

“Thanks,” he replied, embarrassed.

Once he had dried himself off, he went about the task of putting the prophylactic on himself, but he was having difficulty. It seemed that the piece of latex wasn’t tight enough and he couldn’t get it to stay in place. He wasn’t sure if he should hold it or if he could let it go, so he tried tugging it higher and he felt a snap.

“Dammit!”

“Are you ok?” Kitty asked, from the other side of the door.

“Um… yeah. I just think I broke the… _thing_. I brought another one though.”

“You’re trying to put it on _now_?” she asked, sounding curious.

“Am I not supposed to?” he asked, confused.

Stupid Michael… He told him to bring one of these things, but didn’t tell him how to use it. He said Jimmy needed to use one if he was going to be with a… whore, because they were filled with diseases. Kitty didn’t seem like that though. Not like a whore at all. She just seemed like a girl, a shy and quiet girl, of course, but just a regular girl. And not at all disease ridden.

“Just come out...” Kitty said, after a moment. “I’ll help you.”

Jimmy froze. He didn’t know what he had expected her to say, but it wasn’t that. He was mortified that he wasn’t able to get a rubber on and even more mortified that the person in the next room was offering to help him. A complete stranger. A girl.

“You don’t need it yet,” she stated. “It will be easier when it’s time. Just throw that one in the bin by the sink and come out.” 

He mentally prepared himself for a moment, before doing as she asked. When he opened the door, Kitty was sitting at the end of the bed. She smiled at him, reassuringly. He walked out of the bathroom, using his hands to shield his genitals from her view, but he needn’t have worried because her eyes never left his. Shyly, she reached out a hand to him. Jimmy thought she wanted him to hand her the new condom, so he placed it in her hand. When she placed the small packet on the bed to her right and reached out to him again, he realized he had been mistaken. He took her hand and sat beside her, on the bed.

“I don’t know what to do,” he admitted, sheepishly.

“It’ll all come naturally,” she promised. “But I can take the lead, if you’d like.”

Jimmy nodded. 

When Kitty started to remove the dressing gown, he put his hand on hers.

“Can I kiss you first?” he asked. 

“Of course.”

When he hesitated too long, Kitty leaned forward and cupped his cheek. She placed a couple of soft, chaste kisses on his lips. Her lips were soft, probably the softest thing he had ever felt in his life. Jimmy had never been kissed this way. He had kissed his former girlfriend Janey but, even when it was good, it always felt, somehow… awkward. Kissing Kitty didn’t feel that way at all.

One of his hands immediately, and instinctively, went to her waist, while the other reached up and threaded the fingers in her hair, relishing the softness of it. When Kitty opened her mouth beneath his, deepening the kiss, he did the same. Jimmy felt the tip of her tongue graze his own and froze. He had never felt this before and didn’t quite know how to respond, but he loved the feeling of it. Kitty’s mouth was very warm, but tasted cool and minty, like peppermint. When he noticed her tongue begin making gentle strokes against his own, he copied the motion, hoping it was the right thing to do. 

His hand caressed her side, sliding over the silky fabric she was wearing. When his hand rode too high and he accidentally brushed the side of her breast, he pulled his hand away, as if he had touched fire.

“It’s ok,” she murmured, taking his hand and placing it directly on her breast. “That’s what you’re here for.”

He squeezed it gently, feeling it through the fabric. He didn’t know what he had expected breasts to feel like, but it wasn’t like this. When he stole glances at the sweaters of the girls he knew, he thought that breasts looked firm and sturdy, as if they didn’t move. He had tried to touch Janey’s breast once, but it was only a millisecond before she had slapped his hand away. Under a cardigan, a dress and a bullet-bra, it had felt stiff, but this… this felt soft and warm and inviting. 

Jimmy pulled back a bit and looked down at where his hand sat.

“Can I…?” he started.

Kitty nodded and pushed the dressing gown off her shoulders, letting it drop behind her on the bed. Jimmy reached out and, with the tip of his index finger, traced where the lace of the negligee met the perfect swell of flesh. Leaning down, he replaced his finger with his tongue and did the same. He was placing gentle kisses in the same place when the fabric dropped and he was suddenly facing a completely bare breast, the first he had ever seen.

He glanced up at Kitty, who gave him a small smile and a nod, letting him know that it was ok to continue. Eagerly, he bent down and, gently, he ran his finger along the edge of her areola, tracing it’s outline. He watched as the dark rose-colored nipple hardened before his eyes. Entranced by what had just happened, he moved to take the peak into his mouth. As if by instinct, he found himself using his lips and tongue much the same way Kitty has used hers when they were kissing, swirling his tongue around the tip, occasionally stopping to give it a gentle suck.

Her skin smelled of the rose soap from the bathroom and he made a mental note to ask her where she bought it. He wanted to buy himself a case, so that he could smell it and think of her whenever he wanted.

Sitting up, he glanced at Kitty before taking her head back into his hands and capturing her lips with his own. This time, she did not have to take the lead. His desire had taken over and he was no longer the shy boy who had walked into the room. He moved to kiss the pale skin of her neck.

“Are you ready?” she asked, softly.

Jimmy nodded. He had long been ready. Kitty reached to her side and opened the packet, drawing out the latex sheath. A strangled gasp escaped him when she wrapped her hand around the base of his penis. He looked at her, embarrassed at the sound he had made and afraid he was going to let go just from her touch alone.

“You bought the right size,” she said, trying to distract him as she unrolled the condom down his length. 

“Is that good?”

“Very good. Sometimes men get too big a size and it slides off at the wrong moment, which is a problem. You’re perfect, though.”

He blushed at that. If anyone in the room was perfect, it was her.

Kitty looked at him.

“I need you to hold onto the rim of this until you’re inside me, ok? Just in case. And then, afterwards, hold onto it again until you’re out.” 

Jimmy’s eyes widened, not certain he could handle following any instructions in his current state. Kitty took his hand and placed it at the base of the condom, where hers had been.

“Just hold it here for now.“

He nodded.

Kitty stood up and her nightgown fell the rest of the way to the floor. She went back to the bed and laid down and he watched as she scooted up to the top of the bed and spread her legs apart. Jimmy was transfixed by the glistening pink flesh that lay between the dark curls. He wanted nothing more than to take several hours and explore every millimeter of what was lying there… However, the throbbing muscle he held in his hand had other plans which involved burying itself as deeply as possible into the area that was currently holding his gaze.

“Come here...” Kitty murmured, reaching her hand out to him.

Still holding onto himself, Jimmy made his way up the bed. Kitty drew her legs up and spread them further apart, so that he could settle between them. 

“Is this ok?” he asked. “Am I squishing you?”

“You’re fine,” she answered.

“What do I do?” he asked, nervously.

Kitty gave him simple instructions and waited for him to enter her. When he didn’t, she met his eyes.

“I’m afraid to hurt you.”

“You’re not going to hurt me, Jimmy,” she said, softly, using his name for the first time.

He nodded and moved forward, slowly. He thought she might make a noise or give him some indication when he should stop, but she didn’t make a sound. When he felt he could go no deeper, he let go of the condom and laid on top of her, trying to keep from putting his full weight on her.

“Are you ok?” he asked, looking into her eyes.

“I’m fine. Are _you_ ok?”

“Never better,” he replied.

“Go ahead,” she urged, softly.

Jimmy pushed forward again, letting out a low strangled sound. He was embarrassed by the noise he had made, but he couldn’t help it. She felt so good. Warm and tight and nothing like what it felt like when he touched himself. He felt as if he could stay inside her for the rest of his life and be perfectly happy, that he would pay her anything in the world if she would simply allow him to live and die right here, between her legs. He had only managed eight or nine strokes before he ejaculated, leaving him thrilled that it had happened, but disappointed that it was over in the blink of an eye.

When he finally caught his breath, he realized lying next to Kitty, who was still on her back and staring up at the ceiling. At some point, she must have pulled the sheet over herself. He didn’t know when he had rolled off of her or how long they had been finished. He did, however, notice that she wasn’t panting the way he was. In fact, she seemed completely unaffected by the entire act.

“Can I ask you something?”

Kitty turned her head to look at him.

“Was I ok? I mean, did I do anything stupid?”

She gave him a small smile and shook her head.

“You were just fine. You did everything right, nothing stupid at all.”

Jimmy grinned and blushed, and hid his face, making Kitty smile even wider. He really was a nice kid.

“You are so beautiful,” he smiled. “I’m going to remember this moment for the rest of my life.”

Kitty didn’t respond, but looked back up at the ceiling. 

“Kitty... can I ask you one more thing?”

“Yes,” she turned her head towards him again.

He rolled toward her, so that his face was just a few inches from hers. Moving close to her ear, he whispered, as if they were sharing a secret.

“I have three dollars left in my wallet. What can I get for that?”

He pulled back to look at her face. Her eyes were wide and she looked as if she had just won the lottery. Kitty immediately pushed Jimmy onto his back and moved toward him. 

“I’ll show you,” she said, before starting to kiss her way down his torso.


End file.
